Ryan’s notes

Freedom is choosing (to be less free)

Sometime in middle school, I decided I’d make enough money to never need to work doing something I didn’t love. I saw parents all around me work in jobs they complained about, and I decided that would not be me. This has been a key motivating factor for me in work and I’ve been lucky enough to achieve a large degree of financial freedom. I recently left the company I founded six years ago and have ample time to sit and contemplate what to do next, knowing that I hold a coveted set of skills and have plenty of choice.

This is the situation I’d always hoped for: to have the ultimate freedom to choose. But if what you want is the freedom to choose, well, maybe you don’t know what you actually want. What I’ve found is that having more degrees of freedom can actually make it harder to move. This freedom can feel worse than striving for it, much worse, because there’s less direction and purpose in it.

People often ask: “What would you do if you weren’t afraid to fail?” Or, “what would you do if you weren’t afraid of other peoples’ opinions?” Do you actually know the answer to this question? I don’t know. Freedom is only worth something if you know, otherwise it’s a pit of time that you spend doubting, comparing, brooding, waxing nostalgic… floating through space.

Actual freedom is a test of self-confidence. Do you know what’s worth doing? Can you decide to do X and give up A-Z? To know what you want requires knowing and believing in your principles: what are they?

Freedom is about having the confidence to choose. Ironically, choosing means to make commitments and to eschew the other possible paths (to be less free).